Its finally time to share some behind the scenes of what might have been my favorite vacation destination of all time! I am so thankful to my friends Mary Shea & Nick for sharing their little piece of paradise with me! I’m already itching to plan another trip back!  Leading up to this trip I had so much overwhelming anxiety about being away from work, about not being available for my business, leaving my computer behind, and allowing myself to operate without a schedule… It wasn’t perfect. I still spent a few quiet mornings taking in the ocean breeze and brainstorming blog content, client workflows, and day dreaming about upcoming business ventures… But that did not feel like work, it felt like peace! 

I spent 5 days in the Caribbean sun with multiple layers of sunscreen exploring all the island had to offer, sipping on pina coladas and eating way too many empanadas. I got to swim with a few sea turtles and a suspicious sting ray… hike through old historic lighthouses and fall in love with the colorful architecture in Old San Juan! Keep scrolling to see so many of my favorite moments and a few key takeaways!


The very first day in town we we cruising on our golf cart and stopped by a small jewelry cart parked on the side of the road, the sign read “ some day’s were open, other days we’re closed”.. this was the epitome of our trip! Every local business operated on their own schedule, closing down shop for dinner with the family or taking an afternoon break to enjoying the beach. Instead of getting frustrated if the day didn’t go exactly as planned or we couldn’t instantly get a snack from our favorite spot, we would just move on to the next destination or spend an extra hour on the beach. If only this mentality carried over into the states, can you imagine if Starbucks decided to close down for a few hours… cue the panic 🙂


Note to self… maybe I will invest in a Jeep next time I visit Culebra! The island is only about 7 miles long so we opted for the cheaper and fuel efficient golf cart as our catty for the week. This made for quite a few close calls trying to chase down sunset on dirt roads, narrow ledges and fighting over who had to sit in the backwards extra bumpy seat! It made every car ride full of laughter and a little bit of fear.. don’t get me wrong we lucked out in a larger more robust golf cart, but that also meant our driver Nick was more overly confident about its terrain abilities!  BUT if you are planning to do any off road exploring, I would suggest investing in a real 4 wheel drive vehicle!


We adventured to a few different spots around the island and on day 3 we took a rollercoaster boat ride to Culebrita…this uninhabitated island was full of clear blue water, colorful coral and quite a few goats. There was a moment when we are walking across the coastline, climbing over rocks to get to the natural baths listening to the sound of the rushing water through the shells.. it was the most incredibly pure sounds, I wish I could have found a way to bottle it up and listen to it when I’m stressed, but we all just stopped talking in amazement and continued walking in silence. There were so many moments like this on our trip, including the last day. We had just gotten back from a late night dinner and were hoping to prolong packing and our 5am wakeup.. we decided to walk out to the beach one last time… in the pitch black coast line on Flamemco Beach we stared up at the sky to see more stars than I have ever seen in my life, it was overwhelming. We spent the next hour debated planets vs stars vs constellations and catching a glimpse at a few shooting stars, it was the perfect end to our time in paradise!


Our final day we caught the early morning ferry to Old San Juan to do some exploring before our flight, along the way we stopped into a handmade hat shop and fell in love with the business owners, learning about the materials and the story behind all of their products. It was such a different experience than just buying a $30 fedora from Target! Nick and I both walked away with a new addition and couldn’t be more excited to show them off in the colorful streets of Old San Juan!

I don’t want to give away all of the secrets, because this island is too perfect to be overcrowded by tourists.. but SERIOUSLY 10/10 would recommend! Its the perfect balance of low-key island exploration, local cuisine, and natural beauty. I may or may not already have started planning for Mary Sheas 30th birthday celebration back in Culebra 🙂

Island Getaway | Culebra, Puerto Rico

Apr 18, 2019

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I'm Heather, a Wedding & Brand Photographer serving Central Virginia & Beyond! I love sharing beautiful love stories, inspiring wedding details, and practical tips for a stress free wedding!

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